Aniline → 2-(Benzo[b]thiophen-3-yl)-2-(phenylamino)acetic acid

HRID 1044061Notes

Reaction equation

HRID 1044061 reaction equation
[S:1]1[CH:5]=[C:4](B(O)O)[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O.O=[CH:22][C:23]([OH:25])=[O:24]>CC#N>[S:1]1[CH:5]=[C:4]([CH:22]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:23]([OH:25])=[O:24])[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2

Participants

5

Reactant 3

HCID 6115AnilineHCID 2776344(1-Benzothiophen-3-yl)boronic acidHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 585569682-(Benzo[b]thiophen-3-yl)-2-(phenylamino)acetic acidYield 48%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

Benzo[b]thiophen-3-ylboronic acid (387 mg, 2.17 mmol), aniline (202 mg, 2.17 mmol), and 2-oxoacetic acid hydrate (200 mg, 2.17 mmol) were dissolved in CH3CN (12 ml) and stirred in a microwave reactor at 100° C. for 1 hour. The solvent was evaporated, and the residue was dissolved in EtOAc and washed with sat. NaHCO3. The pH of aqueous phase was adjusted with 2N HCl to about 7, and the product was extracted with EtOAc. The organic phase was dried with Na2SO4, filtered and evaporated to obtain 2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetic acid (295 mg, 47.9% yield), which was used in the next step without any further purification.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with sat. NaHCO3
  4. extractionthe product was extracted with EtOAc
  5. dry with materialThe organic phase was dried with Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-6097c3b0f83f454bbd732921f1aa63d7
Source dataset
uspto-grants-2013_10
Patent number
US08563577B2

Reaction notes

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